Shelter Island Holidays from £953

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Your Shelter Island Holiday

Lock in a Shelter Island holiday package that includes everything you need and nothing you don't. Great for views, fishing and nature, consider basing yourself in the neighbourhood of Orient Point. If taking in sights is on the cards during your trip to Shelter Island, check out top attractions like 67 Steps Beach, Railroad Museum of Long Island and Kontokosta Winery. Whatever your travel plans or the size of your budget, organising a tailored Shelter Island holiday is a cinch with Expedia.

Top Shelter Island Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Robert Treat Hotel

Robert Treat Hotel

3 out of 5
Downtown Newark
per person
21 Oct - 24 Oct
found 10 hours ago
Return flight included
London (LHR) to Newark Liberty Intl. Airport (EWR)
7.6/10 Good! (2,427 reviews)
Absolutely wonderful I enjoyed my stayed

Reviewed on 1 Aug 2025

Hampton Inn Long Island / Commack

Hampton Inn Long Island / Commack

2.5 out of 5
per person
21 Oct - 24 Oct
found 10 hours ago
Return flight included
London (LHR) to New York (JFK)
8.8/10 Excellent! (1,007 reviews)
I am not sure why this hotel receives such superlative ratings. It is serviceable, sure. But it's not cheap, the room smelled terribly of disinfectant, and the bed was mediocre, with pillows that felt pounded into submission by thousands of heads. I was not impressed.

Reviewed on 28 Jul 2025

Renaissance Newark Airport Hotel

Renaissance Newark Airport Hotel

4 out of 5
per person
21 Oct - 24 Oct
found 10 hours ago
Return flight included
London (LHR) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,003 reviews)
Nice place easy access and shuttle service

Reviewed on 1 Aug 2025

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
per person
21 Oct - 24 Oct
found 10 hours ago
Return flight included
London (LHR) to Newburgh (SWF)
9.2/10 Wonderful! (916 reviews)
Used for a business trip. Provided all I needed.

Reviewed on 28 Jul 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
21 Oct - 24 Oct
found 10 hours ago
Return flight included
London (LHR) to Newburgh (SWF)
8.2/10 Very Good! (654 reviews)
We stayed at this hotel because it said they had a pool. The pool was closed the whole time. They should have put this on their website. They said they clean rooms every other day. However, I had to ask at the front desk on the every other day and she said we "requested" it. It took forever for someone to come to the front desk and to answer the phone many times.. We won’t be staying at this hotel again

Reviewed on 21 Jul 2025

Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
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Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Sunset Beach and Crescent Beach.

Find hotels in Menantic Creek

Shelter Island Beach Holiday

There's nothing that can beat a Shelter Island holiday. Whether you're enjoying refreshing margaritas at a local hot spot or reading your favourite book by the ocean's edge, your trip to Shelter Island is the time to live out your beachy dreams. Many will suggest you stay close to Wades Beach, situated just 1 mile from downtown. However, you'll also discover a fantastic range of Shelter Island holiday deals around Menhadden Lane Beach and Shell Beach, two other well-liked nearby options.

Shelter Island Essential Information

Language
English
Currency
U.S dollars
Population
1,350
Max Temp Winter
4ºC
Max Temp Summer
24ºC
Top Sights
East Hampton Main Beach, Wolffer Estates Vineyard and 67 Steps Beach

Top hotels in Shelter Island

Marram

Marram

4 out of 5
21 Oceanview Terrace, Montauk, NY
The price is £426 per night from 2 Sept to 3 Sept
£426
2 Sept - 3 Sept
includes taxes & fees
8.6/10 Excellent! (192 reviews)
"We really enjoyed our stay at Marram and would return in the future. The beach is beautiful and they have more than enough chairs and umbrellas to go around. Staff was friendly and helpful and the property was very well maintained. The location is great and easily walkable to most areas. They have ..."

Reviewed on 28 Jul 2025

Marram
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

3 out of 5
727 Old Montauk Highway, Montauk, NY
9.2/10 Wonderful! (557 reviews)
"Absolutely loved our stay. I can’t wait to go back next year!"

Reviewed on 31 Jul 2025

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Beachcomber Resort at Montauk
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd, Montauk, NY
8.4/10 Very Good! (999 reviews)
"I have come here for a while and is the best place to stay in mtk. A little outside of the main areas but you can’t beat the pool."

Reviewed on 24 Jul 2025

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Montauk Yacht Club
See all 4,754 properties in Shelter Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Popular places to visit

Shelter Island Historical Society

You can spend time browsing the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums.

Shelter Island Historical Society

Havens House

You can spend an afternoon studying the exhibits at Havens House during your travels in Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.

Havens House

What to do in Shelter Island

Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

£103
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
Join a small group full-day wine tour with a certified Sommelier host

Long Island Wine and Food Day Trip with Sommelier host from NYC

£110
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
See all activities in Shelter Island

Frequently asked questions

How much does a Shelter Island travel package cost?
Starting from just £953, a travel package is your ticket to affordable travel. Customize your Shelter Island trip by choosing from our great range of airfares, hotels and rental cars.
If I'm not able to travel, can I cancel my Shelter Island travel package?
Your situation can change suddenly, so yes, you can. You may be able to cancel or alter your Shelter Island travel package at no cost within 24 hours of booking. For bookings made more than 24 hours ago, you can still cancel or make changes, but your car rental company, hotel or airline may impose a charge. Need more information? Have a look at our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.
How do I get a cheap travel package to Shelter Island?
One of the easiest ways to save cash (and time) is to combine your bookings with Expedia. Flights, hotels, rental cars and activities — we've got everything you need. Pick and choose a combination that suits you and see your savings stack up. Of course, a package deal is never a one-size-fits-all. That's why we offer more than 550 airlines and 1,000,000 properties globally, which lets you customize your Shelter Island holiday.
Does Expedia offer Book Now, Pay Later Shelter Island holidays?
Expedia has joined forces with online lender Klarna to make your next trip easier on your budget. Paying in instalments means you can spread the costs of your next adventure, leaving you with more cash to spend while you're away. Klarna has several payment plans to choose from, so you're sure to find one that fits into your budget. Browse these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's easy monthly instalment plans. If paying small amounts each month sounds right for you, pick this option during the checkout process.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then check out this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan from Klarna.

What are the top hotels in Shelter Island?
People heading to Shelter Island often book a room at Waterfront House With Dock And Private Beach or Lovely Shelter Island Cottage With Panoramic Bay Views. You'll find them in Silver Beach. Another happening neighbourhood is Hay Beach. Waterfront House With Dock And Private Beach and Tranquil Resort Style Retreat With Luxury Gunite Pool 2 Min From Sandy Beaches are reputable choices in this part of town.
How far in advance should I book my Shelter Island holiday?
While prices do change, we generally suggest booking your spot as soon as possible. Many international airfares are available on Expedia up to a year in advance. If circumstances have left you booking last minute, you might still be in luck. Cheap tickets to Shelter Island sometimes appear just weeks before departure.
What does an Expedia Shelter Island travel package include?
From flights and hotels to rental cars, Expedia can help you put together a Shelter Island package that's right for you. Holidaying for a while? Consider a hotel, flight and rental car bundle. If your break is short, a hotel and airfare deal could suit you better. Activities can also be added once you've made your booking. Our packages make it easy to plan and save.
What should I know before booking a Shelter Island travel package?
Whether it's adventure or relaxation you're craving, a Shelter Island travel package lets you organise your escape your way. Plus, you'll score great discounts when you combine your hotel with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Shelter Island Expedia travel package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines all over the world. Our travel packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.